r/Sissy • • Aug 14 '26

Mod Post Our stance on intolerant behavior and dealing with delicate topics NSFW

22 Upvotes

Hi everyone,

Due to some incidents in recent months, we'd like to clarify our Rule 2 and our stance on intolerant behavior in this community. We'd also like to take this opportunity to clarify our stance on edgeplay topics and how they are handled in a safe and consensual way.

We're a kink community, and a lot of what happens here is intentionally edgy, provocative, and rooted in power dynamics. Humiliation, degradation, and strong language can be part of consensual roleplay and fantasy, and that's not going to change.

At the same time, we need to be clear about where kink rhetoric ends and real-world intolerance begins.

What is allowed

Within the bounds of our rules and when clearly framed as fantasy / roleplay:

  • Kink-typical language around power, submission, and degradation (e.g. "worthless sissy", "owned", etc.)
  • Discussions about kink dynamics, including those that involve race, gender, or sexuality as kink themes, as long as they:
    • don't target real people or groups outside the scene,
    • don't present stereotypes as truth,
    • and stay within the realm of consensual fantasy.
  • General discussions about kink, identity, and experiences, even when they touch on difficult topics, with some limitations to edgeplay (i.e. CNC, blackmail, exposure, extreme violence, etc.; see additional notes below).

What is not allowed

We do not allow content that crosses the line from kink into real-world discrimination or harm. This includes, but is not limited to:

  • Denying or pathologizing identities
    • Statements that devalue or deny other people's identities, orientation, heritage, etc.
    • Framing real identities (trans, nonbinary, etc.) as "just a kink" or "mental illness".
  • Dehumanizing real groups
    • Racist, transphobic, homophobic, misogynistic, or other discriminatory statements presented as fact, not as part of a consensual scene.
    • Using stereotypes about race, gender, or sexuality as if they were true descriptions of real people.
  • Harassment and targeted attacks
    • Insults, threats, or demeaning language directed at specific users or groups outside of a clear roleplay context.
  • Blurring the line between kink and reality
    • When it becomes clear that someone is not engaging in roleplay or fantasy, but is expressing genuine discriminatory beliefs about real-world groups, that content has no place here.

Additional notes: Edgeplay (CNC, blackmail, exposure, extreme violence, etc.)

We allow meta-discussions about edgeplay kinks, including:

  • Sharing experiences ("I have this kink, does anyone else?"),
  • Asking questions and discussing risks / boundaries,
  • Safety tips on how to explore these kinks more safely.

When discussing these topics, descriptive language is ok, but graphic / erotic detail is not. If your post/comment reads more like a story than a discussion or safety guide, it probably crosses the line.

Not allowed:

  • Content that glorifies or romanticizes these kinks (e.g. framing them as "what everyone really wants", "the purest form of kink", etc.).
  • Posts / comments that actively seek partners to act out these kinks in real life (e.g. "Looking for someone to expose me", "Who wants to blackmail me?").

Why this matters

Many of our users are trans, queer, or exploring their gender and sexuality through this kink, and while we are primarily a kink subreddit, we still want to be a place where all of our users feel safe and at home. Content that denies their identities or frames their existence as negative is not just "edgy kink talk", but it actively harms people in this community.

We will remove content that crosses these lines and take action against users who repeatedly engage in this kind of behavior. Our goal is not to police fantasy, but to make sure that fantasy stays fantasy and doesn't become a cover for real-world intolerance.

Quick self-check

If you're unsure whether something crosses the line, ask yourself:

  • Is this clearly framed as fantasy / roleplay?
  • Does this target real people or groups outside of a consensual scene?
  • Would this make someone feel unsafe or unwelcome here because of who they are?

If the answer to any of these points raises concerns, it probably doesn't belong here.

Thank you for understanding. If you have questions, feel free to comment below or contact us directly through modmail.

 


r/Sissy • • Jan 30 '25

Mod Post Political posts NSFW

38 Upvotes

There have been quite a few posts in the past few weeks and months, that were discussing political topics, especially surrounding the US Presidential elections.

While we understand that this has a major impact on the lifes of many members here, it also sparks a lot of passionate and heated discussion. And while we certainly welcome any form of discussion, it still has to be done so in a constructive and civil way, no matter how different other people's views may be from your own.

Since in those posts and in a few posts in the past things have derived from being exactly that, we have come to the conclusion to ask you to stop posting any political posts on /r/sissy. We understand that politics have a major influence on the LGBTQ+ community and therefore by extend on sissies all over the globe, but we feel like this is not the right place to discuss this, as it can become too controversial. We may allow discussing those things again at some point in the future, when we can ensure that it can be done in a way that works for everyone, but for now we feel like it is best to keep those sort of discussions outside.

We have always gone by the rule of "Don't be a dick!" and that is a rule we stand by and it is a rule that is free of politics, religion, gender, sexuality, race or other factors other than just being a decent human being who is open to other people's views and way of lifes and who doesn't shame, insult or threat others, even if they do not represent what they stand for. So as long as you follow that simple rule, everyone is welcome in this community.

Therefore keep in mind that ultimately we are one community and there is already a lot of separation going in in the world, so let's not add to it here.

That being said, we have closed the recent three politics posts from the last hours and will keep them closed. We will also investigate to thoroughly check for any rule violations which there are plenty of on both sides of the fence. This will probably take a day or two, so expect that this will be dealt with in accordance to our rules.


r/Sissy • • 10h ago

Question Experience with SissyLover Academy? NSFW

18 Upvotes

So years ago I found this "academy" to help feminize/sissify me and it was to take occur over time to create consistency and long term affirmations while guiding further into sissification and feminization.

I was NOT consistent with it at all, but lately I started thinking about it again and maybe trying again from scratch.

So my question for all is, has anyone done this with consistency? Is it worth it to try again and be actually committed to it? Is there anything out there that is better? What are some of your thoughts or experiences on this?


r/Sissy • • 20h ago

Discussion What’s your “yeah… that was a bit much” post-orgasm regret moment? NSFW

97 Upvotes

Alright, post-nut clarity is properly wrecking me at the minute. The second I finish I just want to chuck everything in the bin and pretend none of it happened.

Trying to lean into it so it stops hitting so hard every time 😂

We’ve all got one of those moments where it felt unreal while it was happening… then the second you came your brain went “what the hell was that?”

Mine was the night I decided to spit-roast myself with two dildos. Got completely carried away, moaning and talking dirty to myself like I was putting on a show. Came hard… then the silence hit and I realised my flatmate was in her room and had probably heard every single word.

Wanted the floor to swallow me.

What’s yours? The one that still makes you cringe a bit when you think about it?


r/Sissy • • 10h ago

Sissy Story Hard Problem NSFW

15 Upvotes

It's incredibly difficult for me to get hard anymore while getting fucked. I can get hard when I pay with myself but when my partners are using me it does nothing. It's actually nice because it fits well in a cage but it has concerned one or two of my partners before. Usually after I explain it they find it hot.

I can still cum. More than once sometimes and it's still sensitive. It's like it knows it's not going into anything more than a fleshlight or a mouth ever again.

Shout out to the partner I had that made himself cum because he loved sucking my limp clitty so much.


r/Sissy • • 7h ago

Discussion Locked up drinking red wine wathcing sex and the city NSFW

8 Upvotes

Living the life lol :) anyone else doing something similar. Would be so much more fun with a guy hehe


r/Sissy • • 8h ago

Sissy Personals Any one down to chat NSFW

8 Upvotes

Looking for friends to chat with me and maybe share their experiences


r/Sissy • • 19h ago

Sissy Story Someone told me I looked very pretty at the mall today. NSFW

40 Upvotes

OMG! OMG! OMG! I walked around in my pink dress for about an hour today, and at one point in time a little old lady told me I looked very pretty. I instinctively thanked her in my normal, deep masculine voice and instantly wanted to die.

This happened about 20 minutes into the excursion; so I powered through the embarrassment. Other highlights of the trip include walking through 2 stores in the mall and trying on a dress in a department store. All while caged with my attached vibrating plug that I would occasionally turn on, including leaving it on the whole drive home.

Overall, an amazing experience which proved to me I can successfully pass when dressed en femme. This mall is a dying mall with very few people. I may have to go to a busy one next.


r/Sissy • • 11h ago

Question All-natural sissy community? NSFW

6 Upvotes

For me being a sissy is purely a sexual kink/preference. I have no interest in making permanent changes to my body, like surgeries or taking hrt, over this. I just like to dress up girly and do anal play on some nights. Maybe some day I could try it with someone together but that’s a question for the future. Currently it’s basically a form of masturbation. That is also why I will keep my sissy side to myself and not tell about it to anyone close to me.

Does a community for likeminded sissies exist? Most of the subreddits are full with transgender content and hrt advocating which is fine if you are looking to transform yourself but for me it’s not something that I can take inspiration from. What I’m looking for is pretty much like r/femboys4real but for sissies. Something where I could take realistic inspiration from and set achievable goals.


r/Sissy • • 56m ago

Discussion Accidentally burned my clitty NSFW

• Upvotes

So i accidentally spilled some scalding hot coffee on my crotch and while it hurt like crazy I found it made it easier for some backdoor play. When I came recently it felt like buckets. That's one upside the other is that it has made my clitty super sensitive while it grows back the nerve endings. Do I recommend it? ABSOLUTELY NOT!!! THAT SHIT HURT SO MUCH!!!! Would i do it again? NO! Do I think i am going to be cumming from anal play? Maybe but god when I do finally cum again I know I am going to be leaking something crazy.


r/Sissy • • 1h ago

Question Good app NSFW

• Upvotes

Do you know any good app ecxept grindr for fling or any site i could find périple, im from Québec just so it can help


r/Sissy • • 13h ago

Question where can I get captioned? NSFW

8 Upvotes

I have tons of hot vids of me fucking my dildos and I’d love it so much if I was captioned and saw myself featured in a random hypno video. Any suggestions? Are the subreddits for that? or websites? ppl who enjoy making them?


r/Sissy • • 7h ago

Need Help / Advice Which cage would you choose for long term chastity? NSFW

2 Upvotes

Wanting to perma lock myself I dont know if i should take my flat cage which is perfect in almost every aspect but you gotta unlock to pee and clean so no "true perma lock" possible

or

my cobra nub cage which is less comfortable and less practical or cute but i dont need to unlock theoretically.


r/Sissy • • 13h ago

Question Sex Machine recommendations for my birthday NSFW

4 Upvotes

It's my birthday and I would love to finally have one! Looking for recommendations (in EU)
Are there any good reasonably prices machines? I would like a hismith but the average one ends up costing around 500e
I saw some recommend FREDORCH but those with the right attachments can go for nearly 400 which isnt much less than the hismith, maybe im looking in the wrong places?


r/Sissy • • 1d ago

Discussion Is Loctober rewiring everyone else's brain or just mine NSFW

48 Upvotes

Before loctober began I would only able to lock myself up for a day or two at most, but since giving my keys to my wonderful roommate after she asked if she could be my keyholder, I've noticed some changes.

At the start I was just horny, I wanted out of the cage and I just wanted to jerk, but after 3 or 4 days I just wanted goon, I was watching porn for hours on end. My roommate gave me some of her toys (a pair of dildos and a vibe) and that has only accelerated things, I'm now soo desperate for an orgasm, but I havent even thought about my dick, all I can think about right now is fucking my ass, soo much so that I have arranged to meet up with a guy on the weekend just to get so I can get a nice hard fucking, I've even bought lingerie for the occasion.

Its just soo crazy to me that this has happened soo quickly, I just thought that I was locking my cock in a cage for a month, not rewiring myself into a slutty little sissy within 2 weeks, I don't know what the rest of locktober has install for me but I'm excited all be it a lil nervous.


r/Sissy • • 1d ago

Sissy Story Pegged Tiffany last night and she didn't expect to sissygasm out of nowhere. We were both extremely surprised and got caught off guard. NSFW

108 Upvotes

Locktober is still here and Tiffany is securely locked. It's been a while since our strap-on didn't get some action and I wanted to have some fun. Tiffany was in the mood also and we ordered takeout so we can eat after fucking.

I had her on all 4 and flipped her over. Obviously I had her dressed up full woman mode and that fucking whore was just begging for it when my strap-on was sliding inside her. I very much pointed it out.

I flipped her over and slid a pillow under her hips to hit her spot better. I gotta admit that I went pretty hard and fast intermittently to mess with her. About halfway through, something shifted after a few deep and rapid strokes. Her breathing changed and she started gripping the sheets. Then her eyes went wide, like she could suddenly feel it rushing up on her and couldn't believe it.

Her mouth fell open, gasping, and she managed to get out "I'm cumming, I'm cumming!" just before her legs started shaking and she went. Full sissygasm, still locked, completely out of nowhere. Her eyes rolled back as it hit her, wave after wave, and there was no doubt it was a big one.. At first it just started oozing out and after a couple pulses she shot 2 thick ropes of cum.

She looked up at me totally stunned, like her body had gone rogue on her. I stopped and asked what happened, and she told me she had no idea it was coming. No warning, no buildup, nothing. For someone who knows her body as well as she does, that never happens.

So of course I started moving again, slowly, and she admitted she didn't feel it coming at all, but it felt incredible. Wanting to mess with her I scooped some of her cum with my fingers and told her to eat it which she gladly did.

When we finally finished, we just lay there staring at each other, completely flabbergasted. Neither of us could quite believe what had happened. After all this time and all those sessions, her body still found a way to surprise us both. We kept bursting into laughter every few minutes, replaying it, still in shock.

Obviously I had her unlocked and cleaned and she was locked once again. That absolutely made my day seeing her cumming like a slut. It's a first for her to sissygasm prematurely lol.


r/Sissy • • 12h ago

Need Help / Advice Caged, horny and home alone looking for advice on what to do NSFW

2 Upvotes

As the title says, stuck at home caged and horny today. Looking to go deeper as a sissy and explore more but not sure what that would look like. Just looking for some ideas :)


r/Sissy • • 9h ago

Need Help / Advice New sex life NSFW

1 Upvotes

My girlfriend who I’ve been dating for 3 months just found out she has herpes. Obviously sex for us is going to change very differently and maybe even stop. I was wondering what some things we could still do safely would maybe do. She doesn’t know about this side of me I’ve kind of joked about her pegging me and she didn’t seem the most interested although she did seem to want to finger me and almost did after rimming my hole with her finger. We’re going to take time obviously but I’m wondering if there’s a decent way to introduce the idea of a more domme sub role. Any and all ideas welcome.


r/Sissy • • 15h ago

Need Help / Advice Fuck machine advice NSFW

3 Upvotes

Maybe a bit know topic already but what are your ideas or advice on buying right thrusting sex/fuck machine? I would like to get something sturdy or proper that has power. Noise is not a problem. Also might be interested in something that be controlled online/over distance or over calls/streams. Not extremely expencive but can spend. Right now have looked into Hismith Pro Mini or Pro 1, also looking at Lovesense Sex Machine and Mini version. So what are your experiences and reccomendation on that front?


r/Sissy • • 1d ago

Sissy Story 10 years of being a sissy NSFW

37 Upvotes

I wanted to share my experience being a sissy for the past 10 years to inspire other sissies and and honestly its so hot reliving these memories 😂

It started when I was 18. I had always been skinny, smooth, and pretty hairless. I had been surpressing my sissy side for a while but I was finally an adult and wanted to give it a try and see if I liked it. I shaved my body, moisturized, and put on some panties and made a craigslist ad (this was 10 years ago lol) and I remember how nervous I was when my first daddy replied wanting to meet me, I was practically shaking, but less than 2 hours later I was on my back in a public park at night taking my first dick. He was big, at least 7" and it hurt at first and I wasnt sure if it was for me, but after he filled my insides with cum for the first time I knew I would never be the same and that I'd be a cock addicted slut forever. He would be the first of the many men I would give myself to. I would meet with him usually once or twice a week for months. I remember the first time I swallowed cum, how surprised I was at how quickly and eagerly I swallowed it and how much I loved it, how good it made me feel when it was flooding my mouth and how proud I felt when it covered my face. I was worried i'd find cum gross, but I ended up falling in love with it.

I became addicted. I wasn't even attracted to men, but eventually I started looking at random men in public and my first thought would be "I wonder how big his dick is"-- all day every day I would think about dick and cum and how good it felt being used like a toy and how much I wanted that again. So I did what any good sissy does and started looking for men to serve, and boy did I find them. The best part of being a young skinny sissy is that every man secretly wants to use you like a fleshlight :3

The second daddy had a gloryhole, and would fuck my face every time and really taught me how to deepthroat like a slut and to always swallow. I met with him probably a dozen times, sometimes he would breed me and leave me leaking on the drive home. Later I would move into my own apartment and would invite men over all the time, letting them facefuck me and breed me. I remember one night where I had a gloryhole setup and serviced 3 men back to back (Sadly not at the same time). I swallowed the first and second, and the third went in my tummy. I also remember when I first discovered adult theaters, it was like a dream come true. I remember how slutty it felt being on my knees in those dark rooms, sucking on a stranger when a second man walked up and pulled out his throbbing BWC and stuffed it in my mouth too. I've taken loads from so many men at this point I have to think hard to remember some of them.

I used to be shy and would want to avoid getting too intimate with men, I'd really just want to show up and be their toy and then leave, I remember getting uncomfortable with dirty talk at the beginning and finding it awkward, getting post nut clarity and losing interest, but over time as I became more and more of a slut I found myself calling them daddy, begging them for their cock, telling them how i'm their little slut, teasing them and acting cute around them, begging them to give me more cum after i've already taken their load. It's like every cock that I serve makes me more and more of a sissy, and its only gotten stronger over the years. I think once I took my first load I knew deep down that I was meant to be a slut. The feeling of being breeded by a huge load, balls rubbing on my face, cock pumping my throat, I wouldn't trade that for anything.

My advice to any young sissies or those just starting to explore their sissy side: Stay safe (PrEP, Doxy, condoms, etc) trust your gut, and take care of yourself, and once you find a daddy, just relax and enjoy the moment. Remember to respect and love yourself and know that being a sissy does not have to define you if you don't want it to, and that you can ALWAYS say no with something you aren't comfy with.

So after 10 years, i've taken 48 men, and probably 4 times as many loads. I even swallowed one today from a daddy i've already swallowed 4 times in the past month. How did I do? Am I a good sissy :3


r/Sissy • • 1d ago

Sissy Personals Looking to chat- married? NSFW

15 Upvotes

I’ll chat with anyone but am particularly interested in talking to sissies trying to navigate married life. 31 here


r/Sissy • • 12h ago

Need Help / Advice How do i encourage my gf to letting me play? NSFW

0 Upvotes

What do i even do?

A bit of story time incoming because i need a honest opinion and there is background needed.

So I (M19) have introduced my gf (F19) to chastity a couple months ago from now and after some honest chats she started getting more playful with it and a better keyholder overtime, i hope it is not going to stop like that. As currently it is locktober i’m ofc locked but she likes to play with my cock so i will probably get unlocked for her to play. I’m not really aroused by penetrative sex or getting blown although i enjoy it slightly I can’t cum like this, i can only cum while masturbating with my hand.

I was sharing with her lately about my state of mind and the fact that i like the whole crossdressing thing and also i feel great pleasure from playing with my ass. Basically through the chat about it (mainly the crossdressing thing because she thought that the ass thing was not a big deal) she was being very negatively affected bc she immediately started associating it with the fact that i want to be a woman. I don’t, i just like to crossdress bc i feel very submissive and pretty and i like to play with my ass bc it gives me straight pleasure and i also am bi but that’s another level of it that i’m not trying to introduce as i don’t think that she is ready to talk about it. She was clearly mad about it and encouraged me to throw out my outfits and toys. Even tho i tried to explain to her that i absolutely do not want to be a woman she still stayed worried about it.

So my question basically is, how do i encourage her to accept the things i do like to do sexually or maybe even introduce them to our mutual sex life? i really enjoy being in chastity with her, she even lately started teasing me by sitting on my cage and humping it or kissing it and sending me much more spicy pics than normally. I enjoy it but am definitely not even close to fulfill my sissy desires or feel pleasure from this side of me. What do i even do to get those things to be real?


r/Sissy • • 1d ago

Question Any common household items that can be used as a butt plug? NSFW

30 Upvotes

Don’t judge me. I was visiting my friend at her college and she had class for a few hours while I chilled in her dorm room, alone, and super horny. I snooped around and found some toys including a butt plug. I tried it while I touched myself and it was amazinggggg. I ofc cleaned it after and everything so don’t worry about that. But I’ve since been thinking about how amazing it was. I live in a strict household and have no way of buying toys like that without someone knowing, so I was wondering if anyone had good suggestions for butt plug substitutes. I’ve used things before as makeshift dildos but I want a plug!! Any ideas??


r/Sissy • • 20h ago

Question Would coconut oil be an alternative to use with my toys? NSFW

4 Upvotes

I've heard that many people use coconut oil as a lubricant and as a good emergency alternative, even for use in water. Could you tell me if that's true or what other emergency alternatives are available?


r/Sissy • • 1d ago

Sissy Story GFs reaction to sissy content NSFW

28 Upvotes

I'm probably overthinking this. Just found this exciting and wanted to share:

A while back, (for a non related reason) I showed my girlfriend a site with femdom content, including some about sissification.

She looked at it closer than I expected and appeared very interested. She even reacted to some of the sissy related content and looked at me amused. It's not like there have been other "clear" signs though.

So I’ve been wondering if she just found the topic funny or exciting herself, or whether she even might suspect something?